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Controlled Synthesis of Well Defined Poly(3‐hydroxyalkanoate)s‐based Amphiphilic Diblock Copolymers Using Click Chemistry
Authors:Julien Babinot  Estelle Renard  Valérie Langlois
Institution:Institut de Chimie et des Matériaux Paris‐Est (ICMPE), Systèmes Polymères Complexes, UMR CNRS 7182, 2‐8 rue Henri Dunant, 94320 Thiais, France
Abstract:A modular synthesis of short chain length and medium chain length poly(3‐hydroxyalkanoate)s‐b‐poly(ethylene glycol) (PHAs‐b‐PEG) diblock copolymers is described. First, length‐controlled oligomers of hydrophobic poly(3‐hydroxybutyrate‐co‐3‐hydroxyvalerate) (PHBHV), poly(3‐hydroxybutyrate‐co‐3‐hydroxyhexanoate) (PHBHHx), and poly(3‐hydroxyoctanoate‐co‐hydroxyhexanoate) (PHOHHx) containing a carboxylic acid end group were obtained by thermal treatment, with molar masses ranging from 3 800 to 15 000 g · mol?1. After quantitative functionalization with propargylamine, ligation with azide‐terminated poly(ethylene glycol) of 5 000 g · mol?1 was accomplished using the copper (I) catalyzed azide alkyne cycloaddition (CuAAC). Well‐defined diblock copolymers were obtained up to 93% yield, with molar masses ranging from 9 900 to 23 100 g · mol?1. All products were fully characterized using 1H NMR, COSY, SEC, TGA, and DSC.
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Keywords:amphiphiles  click chemistry  diblock copolymers  polyesters  poly(3‐hydroxyalkanoate)
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